2-<(1'S)-1'-hydroxy-1'-phenyl-2'-(tosyloxy)ethyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin | 142798-75-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-<(1'S)-1'-hydroxy-1'-phenyl-2'-(tosyloxy)ethyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin
• 英文别名: [(2S)-2-[(2R,4aR,7R,8aR)-4,4,7-trimethyl-4a,5,6,7,8,8a-hexahydrobenzo[e][1,3]oxathiin-2-yl]-2-hydroxy-2-phenylethyl] 4-methylbenzenesulfonate
• CAS: 142798-75-2
• 化学式: C₂₆H₃₄O₅S₂
• 分子量: 490.685
• InChiKey: HBUMDUHFKADKBW-YUKXHEHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-<(1'S)-1'-hydroxy-1'-phenyl-2'-(tosyloxy)ethyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以32 mg的产率得到2-((1'R)-1'-hydroxy-1'-phenylethyl)hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin
  参考文献：
  名称：

  Addition of organometallic reagents to acyloxathianes. Diastereoselectivity and mechanistic consideration

  摘要：

  The addition of methyl- and phenylmagnesium bromide and phenyllithium to 2-(methoxyacetyl)-, 2-[(tri-isopropylsiloxy)acetyl]-, and 2-[(methylthio)acetyl]hexahydro-4,4,7-trimethyl-4H-1,3-benxozathiin and the corresponding 2'-methyl, 2-(triisopropylsiloxy)propionyl, and 2-(methylthio)butyryl homologs has been Depending on the 2'-substituent, the reagent and (in case of the higher homologs) the configuration at C(2'), these reactions may or may not be highly diastereoselective and may or may not yield the product of Cram's chelate rule involving the oxygen moiety of the oxathiane ring. Explanations for the different stereochemical outcome of the various reactions are suggested.

  DOI：

  10.1021/jo00045a032
• 作为产物：
  描述：

  2-<(1'S)-1'-hydroxy-1'-phenyl-2'-(triisopropylsiloxy)ethyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin 在 吡啶 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 48.5h， 生成 2-<(1'S)-1'-hydroxy-1'-phenyl-2'-(tosyloxy)ethyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin
  参考文献：
  名称：

  Addition of organometallic reagents to acyloxathianes. Diastereoselectivity and mechanistic consideration

  摘要：

  The addition of methyl- and phenylmagnesium bromide and phenyllithium to 2-(methoxyacetyl)-, 2-[(tri-isopropylsiloxy)acetyl]-, and 2-[(methylthio)acetyl]hexahydro-4,4,7-trimethyl-4H-1,3-benxozathiin and the corresponding 2'-methyl, 2-(triisopropylsiloxy)propionyl, and 2-(methylthio)butyryl homologs has been Depending on the 2'-substituent, the reagent and (in case of the higher homologs) the configuration at C(2'), these reactions may or may not be highly diastereoselective and may or may not yield the product of Cram's chelate rule involving the oxygen moiety of the oxathiane ring. Explanations for the different stereochemical outcome of the various reactions are suggested.

  DOI：

  10.1021/jo00045a032

文献信息

• Addition of organometallic reagents to acyloxathianes. Diastereoselectivity and mechanistic consideration
  作者：Xu Bai、Ernest L. Eliel

  DOI：10.1021/jo00045a032

  日期：1992.9

  The addition of methyl- and phenylmagnesium bromide and phenyllithium to 2-(methoxyacetyl)-, 2-[(tri-isopropylsiloxy)acetyl]-, and 2-[(methylthio)acetyl]hexahydro-4,4,7-trimethyl-4H-1,3-benxozathiin and the corresponding 2'-methyl, 2-(triisopropylsiloxy)propionyl, and 2-(methylthio)butyryl homologs has been Depending on the 2'-substituent, the reagent and (in case of the higher homologs) the configuration at C(2'), these reactions may or may not be highly diastereoselective and may or may not yield the product of Cram's chelate rule involving the oxygen moiety of the oxathiane ring. Explanations for the different stereochemical outcome of the various reactions are suggested.